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Damon Brown: Great quote, but there is no simple answer — especially after I spent years looking at hundreds of covers! The truth is that the Playboy model has changed from decade to decade. I believe Acocella was focused on the ’50 and ’60s ideal Playboy model. The ’70s brought in tougher, harsher visuals, reflective of the Studio 54 culture and the hardcore competition from upstarts like Hustler and technological changes like VHS porn. The ’80s focused on celebs, particularly Hollywood, and the ’90s through now cultivated the Playmate system.

I believe the same New Yorker article discussed the average body type over the years and even that changed because of changing American tastes and, of course, plastic surgery.

In his very first Playboy issue, Hefner paraphrased the cliche that she should be a saint in the world and a whore in the bedroom. That’s probably the more accurate description, as it’s not necessarily about body types, but about the ideals they represent.

SB: Which cover is your favorite?

DB: Tough call, but I’d say the October 1971 issue featuring the nude African-American model in the white custom-made Playboy chair. From a composition standpoint, there is a great contrast between Darine Stern’s gorgeous dark brown skin and the chair’s stark Playboy ears.

We also have a sort of innocence in the smile and the pose, an innocence that would begin to wash away as we get further into the ’70s and the covers become more provocative and kinky. Finally, it pushed the controversial idea that African-American beauty was equal to white beauty, especially in 1971 when featuring a woman of color on a major American magazine was rare.

DB: It is definitely raw. One of the common criticisms is how modern technology like Photoshop have made Playboy’s already polished style into a parody of itself. You don’t see that here. The sepia tones, the unfiltered gaze at the reader, and the protective pose all point to a natural, almost casual moment. It’s the last thing you’d expect from someone who had been on the cover about a dozen times before.

SB: Why do you think Anderson, who wrote the book’s foreword, holds the record?

It’s important to keep in mind that Playboy Playmates had been around for a few decades, but the organization didn’t start pushing the playmate system until the early ’90s. Anna Nicole Smith, Jenny McCarthy, and Anderson represented a new kind of model, one that would be forever tied to the Playboy brand. These three would appear on the cover multiple times a year, a feat done only by a handful of previous models like Hefner’s ex-girlfriend Barbi Benton and Bo Derek when the movie “Bolero” hit theaters. Anderson definitely gets credit for taking advantage of that fortunate timing. Like the other two major Playmates, Anderson also has a blonde, surgically-enhanced build that fit Playboy’s style at the time.

SB: What sells as sexy has changed over the years. How do you see that reflected in the women’s looks?

DB: Good question, as I believe it is a misnomer that Playboy’s model style hasn’t changed over the years. There are many indicators, but one particularly big one: Chest size. Playboy has always leaned towards busty women — Marilyn Monroe was its very first model — but they usually had a full, curvy body that complemented their chest because they were natural. The mainstreaming of plastic surgery changed the build of the average Playboy model in the early ’80s, shifting it from almost voluptuous women to thin, often tiny women with huge chests. A quick look today at the Playmates today shows the trend.

SB: What cover was most controversial?

DB: Surprisingly I found little dirt on covers that had been banned or taken off of store shelves, which shows how carefully Hefner walked the line between news value and pornography. There was one funny incident with the August 1955 mermaid cover: A piece of algae was supposed to obscure the mermaid’s chest, but a printer screw-up had her exposed. It was corrected in later issues and, believe it or not, didn’t cause much, if any controversy.

DB: Actually, the Marge Simpson issue was a best-seller! When doing the book I consciously didn’t make it a numbers game, though, because a best-seller is relative to how Playboy was selling overall. For example, Playboy was selling more than seven million copies monthly in the ’70s, but doing only a few million today, so it wouldn’t be possible for a Playboy issue today to sell more than an issue in the ’70s because there literally wouldn’t be enough copies printed to do so.

Magazine nerd talk aside, the best-selling issues were often the ones that were repeated, such as the Playmate trinity we talked about earlier, Bo Derek, and even the Marilyn Monroe anniversary issues.

Monroe was featured in the very first Playboy issue in 1954 and she remains just as popular today.

SB: One of the more recent trends is the celebrity cover. What do you see in the future? Digital, interactive covers?

DB: The celebrity cover has been Playboy’s trend for several years, if not a couple decades now, and I think that will continue.

As far as the future, one of the reasons why Playboy’s Greatest Covers is important is that magazine covers will soon go the way of the album cover or the book cover. I’m in that transitional generation that remembers purchasing CDs, read from physical books, and getting magazine subscriptions by sending those little leaflets in the mail. I don’t think magazine covers will become a lost art, but I do think that our definition of what constitutes a magazine cover will soon be different in our post-iPad age.

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Yes, I did read Playboy for the stories (“I’ve lusted in my heart”). If you haven’t seen the terrific documentary on Hefner, I highly recommend it. He’s a favorite target of feminists (like myself) but he was (and is) a progressive figure on the American scene whose major contributions, including the much needed “sexual revolution” of the late 60s and early 70s, are vastly underestimated.

Over-the-top orgasmic action with great special Viagra effects. It’s big, loud and hard in some extreme level. Playboy provides some stimulation for the eyes and ears, the brain gets the shaft. As I believe in the saying, ‘We believe what we want to believe.’ To push suddenly or strongly with a finger or something pointed.